Hydrogen Bromide → 4-(5-Bromo-3-methyl-2-pyridinyl)butylamine

5-Amino-2-(4-aminobutyl)-3-methylpyridine (5.11 g) in hydrobromic acid (48%, 47 ml) was reacted with cuprous bromide (4.98 g) and copper bronze (0.18 g). A solution of sodium nitrite (2.45 g) in water (16 ml) was added at 5° to 8° C. over 45 minutes, the reaction mixture was allowed to stir at 5° to 8° C. for a further hour and then stirred at room temperature for 3.5 hours. The reaction mixture was diluted with water, and hydrogen sulphide gas was passed, while the pH was progressively raised to 11 by the addition of sodium hydroxide solution. The precipitated copper salts were filtered off at intervals during the above procedure. The product was then extracted at pH 11 with chloroform to give 5-bromo-2-(4-aminobutyl)-3-methylpyridine (4.95 g) m.p. 35°-37° C.

1. stirringstirred at room temperature for 3.5 hours
2. filtrationThe precipitated copper salts were filtered off at intervals during the above procedure
3. extractionThe product was then extracted at pH 11 with chloroform

ORD record

ord-7b2a3b6815df478eb40a02b127e535c3

Source dataset

uspto-grants-1984_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04486434